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2D Structure
Also known as: 549-18-8, Amitriptyline hcl, Annoyltin, Tryptizol, Domical, Syneudon
Molecular Formula
C20H24ClN
Molecular Weight
313.9  g/mol
InChI Key
KFYRPLNVJVHZGT-UHFFFAOYSA-N
FDA UNII
26LUD4JO9K

Tricyclic antidepressant with anticholinergic and sedative properties. It appears to prevent the re-uptake of norepinephrine and serotonin at nerve terminals, thus potentiating the action of these neurotransmitters. Amitriptyline also appears to antagonize cholinergic and alpha-1 adrenergic responses to bioactive amines.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N,N-dimethyl-3-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenylidene)propan-1-amine;hydrochloride
2.1.2 InChI
InChI=1S/C20H23N.ClH/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20;/h3-6,8-12H,7,13-15H2,1-2H3;1H
2.1.3 InChI Key
KFYRPLNVJVHZGT-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CN(C)CCC=C1C2=CC=CC=C2CCC3=CC=CC=C31.Cl
2.2 Other Identifiers
2.2.1 UNII
26LUD4JO9K
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Amineurin

2. Amitrip

3. Amitriptylin Beta

4. Amitriptylin Desitin

5. Amitriptylin Neuraxpharm

6. Amitriptylin Rph

7. Amitriptylin-neuraxpharm

8. Amitriptyline

9. Amitrol

10. Anapsique

11. Apo Amitriptyline

12. Apo-amitriptyline

13. Damilen

14. Desitin, Amitriptylin

15. Domical

16. Elavil

17. Endep

18. Laroxyl

19. Lentizol

20. Novoprotect

21. Rph, Amitriptylin

22. Saroten

23. Sarotex

24. Syneudon

25. Triptafen

26. Tryptanol

27. Tryptine

28. Tryptizol

2.3.2 Depositor-Supplied Synonyms

1. 549-18-8

2. Amitriptyline Hcl

3. Annoyltin

4. Tryptizol

5. Domical

6. Syneudon

7. Endep

8. Lentizol

9. Novoprotect

10. Etravil

11. Saroten

12. Elavil Hydrochloride

13. Amineurin

14. Amitril

15. Amitrip

16. Anapsique

17. Tryptine

18. Amavil

19. Amitid

20. Ami-anelun

21. Apo-amitriptyline

22. Daprimen

23. Elatrolet

24. Maxivalet

25. Miketorin

26. Mitaptyline

27. Rantoron

28. Sarotena

29. Trepiline

30. Triptizol

31. Trytomer

32. Vanatrip

33. Yamanouchi

34. Amilit

35. Amiplin

36. Amiprin

37. Amyline

38. Amyzol

39. Belpax

40. Elatrol

41. Enafon

42. Etrafon

43. Kyliran

44. Larozyl

45. Levate

46. Pinsanu

47. Pinsaun

48. Teperin

49. Triavil

50. Tridep

51. Tripta

52. Trynol

53. Damilen Hydrochloride

54. Amitriptyline Chloride

55. Saroten Retard

56. Tryptizol Retard

57. Limbitrol Ds

58. Tryptacap Hydrochloride

59. Adt-zimaia

60. Oasil-m

61. Redomex

62. Proheptadien Monohydrochloride

63. Amitriptyline (hydrochloride)

64. Sk-amitriptyline Chloride

65. Limbitrol

66. Sarotex

67. Nih 10794

68. Ccris 7092

69. Amitryptiline Hydrochloride

70. Nsc-104210

71. 26lud4jo9k

72. Annolytin

73. Mls000028437

74. Component Of Etrafon

75. Component Of Triavil

76. 5-(3-(dimethylamino)propylidene) Dibenzosuberane Hcl

77. 3-(10,11-dihydro-5h-dibenzo[a,d][7]annulen-5-ylidene)-n,n-dimethylpropan-1-amine Hydrochloride

78. 1-propanamine, 3-(10,11-dihydro-5h-dibenzo(a,d)cyclohepten-5-ylidene)-n,n-dimethyl-, Hydrochloride

79. Novotriptyn

80. Nornaln

81. Smr000058368

82. 549-18-8 (hcl)

83. Amitryptyline Hydrochloride

84. 5-(3-dimethylaminopropylidene)dibenzo(a,d)(1,4)cycloheptadiene Hydrochloride

85. Dsstox_cid_13187

86. Dsstox_rid_79055

87. Dsstox_gsid_33187

88. Amitriptyline Hydrochloride 100 Microg/ml In Acetonitrile

89. 1-propanamine, 3-(10,11-dihydro-5h-dibenzo[a,d]cyclohepten-5-ylidene)-n,n-dimethyl-, Hydrochloride

90. 3-(10,11-dihydro-5h-dibenzo[a,d][7]annulen-5-ylidene)-n,n-dimethyl-1-propanamine Hydrochloride

91. 3-(10,11-dihydro-5h-dibenzo[a,d]cyclohepten-5-ylidene)-n,n-dimethyl-1-propanamine Hydrochloride

92. Nsc169910

93. Wln: L C676 By&t&j Bu3n1&1 &gh

94. Amitriptyline Hydrochloride [jan]

95. Sr-01000003046

96. Ncgc00015095-09

97. Cas-549-18-8

98. Einecs 208-964-6

99. Mfcd00012537

100. Amitryptylline Hydrochloride

101. Unii-26lud4jo9k

102. Nsc 104210

103. Amilent

104. Sylvemid

105. Amicen

106. Euplit

107. Uxen

108. 5-(3-dimethylaminopropylidene)dibenzo[a,4]cycloheptadiene Hydrochloride

109. 5-[3-(dimethylamino)propylidene]dibenzo[a,4]cycloheptadiene Hydrochloride

110. 1-propanamine,11-dihydro-5h-dibenzo[a,d]cyclohepten-5-ylidene)-n,n-dimethyl-, Hydrochloride

111. 5-(3-dimethylaminopropylidene)dibenzo[a,d][1,4]cycloheptadiene Hydrochloride

112. 5h-dibenzo[a,.gamma.-propylamine, 10,11-dihydro-n,n-dimethyl-, Hydrochloride

113. 5h-dibenzo[a,.gamma.-propylamine, 10,11-dihydro-n,n-dimethyl-,hydrochloride

114. Prestwick_20

115. 3-(5,6-dihydrodibenzo[2,1-b:1',2'-e][7]annulen-11-ylidene)-n,n-dimethylpropan-1-amine;hydrochloride

116. Drg-0169

117. Elavil (tn)

118. Amitriptyline Hydrochloride [usp:jan]

119. Cpd000058368

120. Opera_id_618

121. Nortriptyline Impurity F

122. Amitriptylini Hydrochloridum

123. C20h23n.hcl

124. Schembl41079

125. 10,11-dihydro-n,n-dimethyl-5h-dibenzo(a,d)cycloheptene-delta(sup 5,gamma)-propylamine Hydrochloride

126. Mls001055393

127. Mls001074176

128. Mls002222152

129. Spectrum1500117

130. Regid_for_cid_11065

131. Chebi:2667

132. Chembl1200964

133. Dtxsid9033187

134. Hy-b0527a

135. Amitriptyline Hydrochloride ,(s)

136. Amitriptyline Hydrochloride, 99%

137. Hms1568o09

138. Hms1920c13

139. Pharmakon1600-01500117

140. Bcp31573

141. Amitriptyline-[13c3] Hydrochloride

142. Tox21_113122

143. Tox21_201278

144. Tox21_303612

145. Tox21_500112

146. Ccg-38919

147. Nsc104210

148. Nsc755869

149. S3183

150. Akos015994716

151. Tox21_113122_1

152. Ks-1291

153. Lp00112

154. Nc00497

155. Nsc-169910

156. Nsc-755869

157. Amitriptyline Hydrochloride (jp17/usp)

158. Amitriptyline Hydrochloride [mi]

159. Ncgc00015095-15

160. Ncgc00024433-03

161. Ncgc00024433-05

162. Ncgc00093609-01

163. Ncgc00093609-02

164. Ncgc00093609-03

165. Ncgc00093609-04

166. Ncgc00093609-05

167. Ncgc00257393-01

168. Ncgc00258830-01

169. Ncgc00260797-01

170. 5h-dibenzo(a,d)cycloheptene-delta(sup 5),gamma-propylamine, 10,11-dihydro-n,n-dimethyl-, Hydrochloride

171. 5h-dibenzo(a,d)cycloheptene-delta5,gamma-propylamine, 10,11-dihydro-n,n-dimethyl-, Hydrochloride

172. Amitriptyline Hydrochloride [hsdb]

173. Ba164159

174. N,n-dimethyl-3-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenylidene)propan-1-amine;hydrochloride

175. Amitriptyline Hcl;nortriptyline Impurity F

176. Amitriptyline Hydrochloride [mart.]

177. Amitriptyline Hydrochloride [vandf]

178. Amitriptyline Hydrochloride [usp-rs]

179. Amitriptyline Hydrochloride [who-dd]

180. Amitriptyline Hydrochloride [who-ip]

181. A0908

182. Eu-0100112

183. Ft-0662108

184. Ft-0662109

185. Sw196337-3

186. A 8404

187. A16404

188. D00809

189. D81789

190. Amitriptyline Hydrochloride [ep Impurity]

191. A854879

192. Amitriptyline Hydrochloride [ep Monograph]

193. Amitriptyline Hydrochloride [usp Impurity]

194. Amitriptyline Hydrochloride [usp Monograph]

195. Amitriptylini Hydrochloridum [who-ip Latin]

196. Amitriptyline Hydrochloride, >=98% (tlc), Powder

197. Sr-01000003046-2

198. Sr-01000003046-6

199. W-105596

200. Etrafon-a Component Amitriptyline Hydrochloride

201. Limbitrol Component Amitriptyline Hydrochloride

202. Q27254112

203. Amitriptyline Hydrochloride Component Of Etrafon-a

204. Amitriptyline Hydrochloride Component Of Limbitrol

205. F0001-1443

206. Limbitrol Ds Component Amitriptyline Hydrochloride

207. Amitriptyline Hydrochloride Component Of Limbitrol Ds

208. 5-[3-(dimethylamino)propylidene]dibenzosuberane Hydrochloride

209. Amitriptyline Hydrochloride 1.0 Mg/ml In Methanol (as Free Base)

210. Amitriptyline Hydrochloride, Drug Standard, 1.0 Mg/ml In Methanol

211. Amitriptyline Hydrochloride, British Pharmacopoeia (bp) Reference Standard

212. Amitriptyline Hydrochloride, European Pharmacopoeia (ep) Reference Standard

213. Amitriptyline Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

214. Amitriptyline Hydrochloride, United States Pharmacopeia (usp) Reference Standard

215. 1-propanamine, 3-(10,11-dihydro-5h-dibenzo(a,d)cyclohepten-5-ylidene)-n,n-dimethyl-, Hydrochloride (1:1)

216. 10,11-dihydro-n,n-dimethyl-5h-dibenzo[a,d]cycloheptene-delta5,gamma-propylamine Hydrochloride

217. 3-(10,11-dihydro-5h-dibenzo[a,d]cyc Lohepten-5-ylidene)-n,n-dimethyl-1-propanamine Hydrochloride

218. 5h-dibenzo[a,d]cycloheptene-delta(sup5),gamma-propylamine, 10,11-dihydro-n,n-dimethyl-, Hydrochloride

219. 5h-dibenzo[a,d]cycloheptene-delta5,gamma-propylamine, 10,11-dihydro-n,n-dimethyl-, Hydrochloride (6ci,8ci)

220. Amitriptyline Hydrochloride Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

221. N,n-dimethyl-3-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenylidene)propan-1-amine;hydron;chloride

2.4 Create Date
2005-06-08
3 Chemical and Physical Properties
Molecular Weight 313.9 g/mol
Molecular Formula C20H24ClN
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count3
Exact Mass313.1597275 g/mol
Monoisotopic Mass313.1597275 g/mol
Topological Polar Surface Area3.2 Ų
Heavy Atom Count22
Formal Charge0
Complexity331
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameAmitriptyline hydrochloride
Drug LabelDESCRIPTIONAmitriptyline HCl is 3-(10,11-dihydro-5H-dibenzo [a,d] cycloheptene-5-ylidene)-N,N-dimethyl-1-propanamine hydrochloride. Its empirical formula is C20H23NHCl, and its structural formula isAmitriptyline HCl, a dibenzocycloheptadiene deriv...
Active IngredientAmitriptyline hydrochloride
Dosage FormTablet
Routeoral; Oral
Strength75mg; 100mg; 25mg; 50mg; 10mg; 150mg
Market StatusPrescription
CompanyVintage Pharms; Mutual Pharm; Sun Pharm Inds; Sandoz; Mylan

2 of 2  
Drug NameAmitriptyline hydrochloride
Drug LabelDESCRIPTIONAmitriptyline HCl is 3-(10,11-dihydro-5H-dibenzo [a,d] cycloheptene-5-ylidene)-N,N-dimethyl-1-propanamine hydrochloride. Its empirical formula is C20H23NHCl, and its structural formula isAmitriptyline HCl, a dibenzocycloheptadiene deriv...
Active IngredientAmitriptyline hydrochloride
Dosage FormTablet
Routeoral; Oral
Strength75mg; 100mg; 25mg; 50mg; 10mg; 150mg
Market StatusPrescription
CompanyVintage Pharms; Mutual Pharm; Sun Pharm Inds; Sandoz; Mylan

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Analgesics, Non-Narcotic

A subclass of analgesic agents that typically do not bind to OPIOID RECEPTORS and are not addictive. Many non-narcotic analgesics are offered as NONPRESCRIPTION DRUGS. (See all compounds classified as Analgesics, Non-Narcotic.)


Antidepressive Agents, Tricyclic

Substances that contain a fused three-ring moiety and are used in the treatment of depression. These drugs block the uptake of norepinephrine and serotonin into axon terminals and may block some subtypes of serotonin, adrenergic, and histamine receptors. However, the mechanism of their antidepressant effects is not clear because the therapeutic effects usually take weeks to develop and may reflect compensatory changes in the central nervous system. (See all compounds classified as Antidepressive Agents, Tricyclic.)


Adrenergic Uptake Inhibitors

Drugs that block the transport of adrenergic transmitters into axon terminals or into storage vesicles within terminals. The tricyclic antidepressants (ANTIDEPRESSIVE AGENTS, TRICYCLIC) and amphetamines are among the therapeutically important drugs that may act via inhibition of adrenergic transport. Many of these drugs also block transport of serotonin. (See all compounds classified as Adrenergic Uptake Inhibitors.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Tricyclic Antidepressant [EPC]